- Marinate the pork: In a blender, purée the chipotles with their reserved sauce, oil, vinegar, chile powder, oregano, honey, and garlic until smooth and season with salt and pepper. Put pork into a 1-gallon resealable plastic bag and pour sauce over pork. Refrigerate overnight.
- Make the mole: Heat oven to broil and position a rack 10" from the heating element. Toss tomatillos, tomatoes, and onions with 2 tbsp. oil in a bowl and transfer to an aluminum foil–lined baking sheet; broil, turning once with tongs, until soft and well browned, about 15 minutes. Transfer charred vegetables to a large bowl; set aside. Heat oven to 400˚. Transfer chiles to the aluminum foil–lined baking sheet and toast, turning once, until dark and fragrant, about 3 minutes. Transfer toasted chiles to large bowl and cover with 3 cups boiling water; set aside to let soften for 15 minutes. Drain chiles, reserving 1⁄2 cup soaking liquid; set aside.
- Heat 3⁄4 cup oil in a 3-qt. high-sided skillet over medium-high heat. Add plantains (or bananas) and cook, stirring frequently, until browned, 2 minutes. Add peanuts and sesame seeds and cook, stirring frequently, until browned, 3 minutes. Add the raisins, the tomatillo mixture, and the chiles with the reserved soaking liquid, along with the chicken broth, chocolate, oregano, canela, and bread; bring the mixture to a boil and remove from heat. Working in batches, purée the chile mixture in a blender to make a smooth mole.
- Heat remaining oil in a 4-qt. saucepan over medium-high heat. Add mole and cook, whisking frequently, until it thickens slightly, about 5 minutes. Season with salt and piloncillo; set mole aside and keep warm.
- Meanwhile, heat oven to 400˚. Remove pork from adobo, season lightly with salt, and transfer to a rack set in a roasting pan. Discard adobo. Cook the pork, flipping once, until browned and an instant-read thermometer inserted into center of pork reads 150˚, about 45 minutes. Transfer pork to a platter; let rest for 10 minutes. Slice pork into 1⁄2"-thick medallions. Divide mole between 6 plates. Arrange pork over mole and garnish with peanuts and cilantro.
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